Theodore Roosevelt was elected Governor of New York in 1898, Vice President of the United States in 1900 and President of the United States in 1904. (He lost the U.S. Presidential Election of 1912.)
Franklin D. Roosevelt was elected Governor of New York in 1928 and 1930 and President of the United States in 1932, 1936, 1940 and 1944. (He lost the U.S. Vice-Presidential Election of 1920.)
TR's first elected office was to the New York State Assembly.
Franklin D. Roosevelt
Franklin D. Roosevelt was elected for President in 1932 and took office in '33.
Roosevelt
He was 42 years old when he became the 26th president. He was 46 when he was elected U. S. President in the fall of 1904.
Franklin Delano Roosevelt
Technically John F. Kennedy was elected the youngest but the youngest president in office was Roosevelt. (Roosevelt was elected Vice President in 1900 and became President when President William McKinley was assassinated.)
Theodore Roosevelt was elected one time in 1904. However, this was his second term in office. His first term came about due to the assassination of William McKinley in 1901.
Four Times
Franklin D. Roosevelt.
Franklin D. Roosevelt 1940.
Franklin D. Roosevelt was elected to a 4th term in 1944. He died in office in 1945.